Functionalized Organoborane Derivatives in Organic Synthesis

Knöchel, Paul; Ila, H.; Korn, Tobias J.; Baron, Oliver

doi:10.1002/9783527619467.ch3

Cited by 9 publications

(12 citation statements)

References 179 publications

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“…Arylboronic esters can be synthesized from aryl halides, triflates, and amines via palladium-catalyzed cross-coupling reactions with tetraalkoxydiborane reagents. − While these conditions tolerate a wide range of functional groups, tetraalkoxydiboron reagents are expensive, and therefore methods for the synthesis of arylboronic esters via trialkyl borates are in demand. Early work by Ley demonstrated various boronic acid esters can be prepared in flow under cryogenic conditions .…”

Section: Mixingmentioning

confidence: 99%

The Hitchhiker’s Guide to Flow Chemistry

et al. 2017

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Flow chemistry involves the use of channels or tubing to conduct a reaction in a continuous stream rather than in a flask. Flow equipment provides chemists with unique control over reaction parameters enhancing reactivity or in some cases enabling new reactions. This relatively young technology has received a remarkable amount of attention in the past decade with many reports on what can be done in flow. Until recently, however, the question, "Should we do this in flow?" has merely been an afterthought. This review introduces readers to the basic principles and fundamentals of flow chemistry and critically discusses recent flow chemistry accounts.

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Section: Mixingmentioning

confidence: 99%

The Hitchhiker’s Guide to Flow Chemistry

et al. 2017

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“…Organoboron reagents have had an enormous impact on the development of new chemical reactions and have extended the scope of accessible complex molecular scaffolds. − Organoboronate compounds are particularly attractive owing to their wide availability and air stability, making them versatile reagents in organic synthesis. , …”

Section: Introductionmentioning

confidence: 99%

“…Organoboron reagents have had an enormous impact on the development of new chemical reactions 1 and have extended the scope of accessible complex molecular scaffolds. 2−4 Organoboronate compounds are particularly attractive owing to their wide availability and air stability, 5 making them versatile reagents in organic synthesis. 6,7 Although many synthetic methods utilize transformations of C−B bonds, 2 the development of polyborylated reagents would enable greater structural diversity, an important objective.…”

Section: ■ Introductionmentioning

confidence: 99%

Stereoselective Diels–Alder Reactions of gem-Diborylalkenes: Toward the Synthesis of gem-Diboron-Based Polymers

et al. 2021

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Although gem -diborylalkenes are known to be among the most valuable reagents in modern organic synthesis, providing a rapid access to a wide array of transformations, including the construction of C–C and C-heteroatom bonds, their use as dienophile-reactive groups has been rare. Herein we report the Diels–Alder (DA) reaction of (unsymmetrical) gem -diborylalkenes. These reactions provide a general and efficient method for the stereoselective conversion of gem -diborylalkenes to rapidly access 1,1-bisborylcyclohexenes. Using the same DA reaction manifold with borylated-dienes and gem- diborylalkenes, we also developed a concise, highly regioselective synthesis of 1,1,2-tris- and 1,1,3,4-tetrakis(boronates)cyclohexenes, a family of compounds that currently lack efficient synthetic access. Furthermore, DFT calculations provided insight into the underlying factors that control the chemo-, regio-, and stereoselectivity of these DA reactions. This method also provides stereodivergent syntheses of gem- diborylnorbornenes. The utility of the gem- diborylnorbornene building blocks was demonstrated by ring-opening metathesis polymerization (ROMP), providing a highly modular approach to the first synthesis of the gem- diboron-based polymers. Additionally, these polymers have been successfully submitted to postpolymerization modification reactions. Given its simplicity and versatility, we believe that this novel DA and ROMP approach holds great promise for organoboron synthesis as well as organoboron-based polymers and that it will result in more novel transformations in both academic and industrial research.

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“…2 Organoboron reagents have had an enormous impact on the development of new chemical reactions and have extended the scope of accessible complex molecular scaffolds. 3,4 Organoboronate compounds are particularly attractive owing to their wide availability and air stability, 5 making them versatile reagents in organic synthesis. 6,7 Although many synthetic methods utilize transformations of C-B bonds, 2 the development of polyborylated reagents would enable greater structural diversity -an important objective.…”

mentioning

confidence: 99%

Stereoselective Diels-Alder Reactions of gem-Diborylalkenes: Toward the Synthesis of gem-Diboron-Based Polymers via ROMP

Eghbarieh¹,

Hanania²,

Zamir³

et al. 2021

Preprint

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Although gem-diborylalkenes are known to be among the most valuable reagents in modern organic synthesis, providing a rapid access to a wide array of transformations, including the construction of C−C and C‐heteroatom bonds, their use as dienophile-reactive groups has been rare. Herein we report the Diels-Alder (DA) reaction of (unsymmetrical) gem-diborylalkenes. These reactions provide a general and efficient method for the stereoselective conversion of gem-diborylalkenes to rapidly access 1,1-bisborylcyclohexenes. Using the same DA reaction manifold with borylated-dienes and gem-diborylalkenes, we also developed a concise, highly regioselective synthesis of 1,1,2-tris- and 1,1,3,4-tetrakis(boronates)cyclohexenes, a family of compounds that currently lack efficient synthetic access. Furthermore, DFT calculations provided insight into the underlying factors that control the chemo-, regio, and stereoselectivity of these DA reactions. This method also provides stereodivergent syntheses of gem-diboryl-norbornenes. The utility of the gem-diboryl-norbornene building blocks was demonstrated by ring-opening metathesis polymerization (ROMP), providing a highly modular approach to the first synthesis of the gem-diboron-based polymers. Given its simplicity and versatility, we believe that this novel DA and ROMP approach holds great promise for organoboron synthesis as well as organoboron-based polymers and that it will result in more novel transformations in both academic and industrial research.<br>

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Functionalized Organoborane Derivatives in Organic Synthesis

Cited by 9 publications

References 179 publications

The Hitchhiker’s Guide to Flow Chemistry

The Hitchhiker’s Guide to Flow Chemistry

Stereoselective Diels–Alder Reactions of gem-Diborylalkenes: Toward the Synthesis of gem-Diboron-Based Polymers

Stereoselective Diels-Alder Reactions of gem-Diborylalkenes: Toward the Synthesis of gem-Diboron-Based Polymers via ROMP

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